Upshaw is Owner/Lawyer with Jessica Sibley Upshaw & Associates. She was previously a Partner/Lawyer with Hopkins, Crawley, Bagwell & Upshaw from 1988-2000. She earned her JD from the University of Mississippi School of Law and BBA from the University of Mississippi.

Upshaw is a member of the American Bar Association, American Legislative Exchange Council, Colonial Dames, Daughters of the American Revolution, Gulf Coast Chamber of Commerce, Gulfport Yacht Club, Harrison County Bar Association, and the Mississippi Bar Association. [1]